Photoreactions of polycyclic aromatic hydrocarbons with N-arylglycines

Abstract

Irradiation of aerated solutions of polycyclic aromatic hydrocarbons in acetonitrile containing N-arylglycines leads to decarboxylation of the acids. Other products include anilines and formanilides. The reaction occurs less readily in benzene solution. Since the amino-acids quench the fluorescence of the hydrocarbons at nearly the diffusion-controlled limit, the reaction is thought to occur from the first excited singlet state of the hydrocarbon. The primary photochemical process is ascribed as the transfer of an electron from the amino-acid to the excited hydrocarbon. The relevance of this electron-transfer reaction to those undergone by triplet excited states is discussed.